Imidazole → HCID 19914911, compound

HRID 1650284Notes

Reaction equation

HRID 1650284 reaction equation
[CH2:1]([N:8]1[CH:12]([CH2:13][OH:14])[CH2:11][CH2:10][CH:9]1[CH2:15][OH:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([N:8]1[CH:12]([CH2:13][O:14][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:11][CH2:10][CH:9]1[CH2:15][OH:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 11206806(1-Benzylpyrrolidine-2,5-diyl)dimethanol

Product 1

HCID 19914911HCID 19914911, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-benzyl-2,5-bis(hydroxymethyl)pyrrolidine (30 g) and imidazole (27.8 g) in dimethylformamide (300 ml) was added portionwise t-butyldimethylsilyl chloride (20.4 g) at room temperature. After stirring for 1 hour at room temperature, water (0.9 l) and ethyl acetate (1.4 l) was added to the mixture. After shaking, aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layer was washed with water (3 times) and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was column chromatographed on silica gel (eluent:nexane/ethyl acetate, 8:2-7:3 V/V) to give 1-benzyl-5-t-butyldimethylsilyloxymethyl-2-hydroxymethylpyrrolidine (16.8 g).

Workup

  1. stirringAfter shaking
  2. customaqueous layer was separated
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic layer was washed with water (3 times) and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customchromatographed on silica gel (eluent:nexane/ethyl acetate, 8:2-7:3 V/V)

Sources & evidence

ORD record
ord-042154f92728477780a92092a35e8c92
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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